反応 #527720

反応方程式

Methyl iodide

Methyl iodide

4-chloro-3-methylphenol

potassium carbonate

N-bromosuccinimide

benzoyl peroxide

→

2-chloro-5-methoxy benzyl bromide

溶媒

acetone

carbon tetrachloride

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture stirred for a further hour
2. 2
   その他Solvent was removed by evaporation
3. 3
   その他the residue partitioned between water and ethyl acetate
4. 4
   その他The organic layer yielded an oil which
5. 5
   温度was heated
6. 6
   温度The mixture was cooled
7. 7
   ろ過filtered
8. 8
   濃縮the filtrate concentrated
9. 9
   その他to give a residue which
10. 10
    workup.DISTILLATIONwas distilled under high vacuum
11. 11
    その他The fractions collected between 88° and 94° C./0.4 mbar
12. 12
    その他were recrystallised from petroleum ether (b.p. 60°-80° C.)

実験手順

Methyl iodide (110 g was added dropwise to a stirred solution of 4-chloro-3-methylphenol (100 g) and potassium carbonate (194 g) in acetone (500 ml). The mixture was stirred for 1.5 hours. Methyl iodide (142 g) was added and the mixture stirred for a further hour. Solvent was removed by evaporation and the residue partitioned between water and ethyl acetate. The organic layer yielded an oil which was heated under reflux for 2 hours with N-bromosuccinimide (119 g) and benzoyl peroxide (1 g) in carbon tetrachloride (250 ml). The mixture was cooled, filtered and the filtrate concentrated to give a residue which was distilled under high vacuum. The fractions collected between 88° and 94° C./0.4 mbar were recrystallised from petroleum ether (b.p. 60°-80° C.) to give 2-chloro-5-methoxy benzyl bromide, m.p. 51°-52° C.

出典